TW200906394A - Tetrahydroindole and tetrahydroindazole derivatives - Google Patents

Tetrahydroindole and tetrahydroindazole derivatives Download PDF

Info

Publication number: TW200906394A
Authority: TW; Taiwan
Prior art keywords: tetrahydro; alkyl; group; benzamide; keto
Prior art date: 2007-04-16

Application number

TW097113864A

Other languages

English (en)

Chinese (zh)

Inventor

Kenneth He Huang

Andy J Ommen

Thomas E Barta

Philip F Hughes

James M Veal

Wei Ma

Emilie D Smith

Angela R Woodward

W Stephen Mccall

Original Assignee

Serenex Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-04-16

Filing date

2008-04-16

Publication date

2009-02-16

2008-04-16 Application filed by Serenex Inc filed Critical Serenex Inc

2009-02-16 Publication of TW200906394A publication Critical patent/TW200906394A/zh

Links

NYOWYNSNCXRVNQ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indazole Chemical class C1=CCC2CNNC2=C1 NYOWYNSNCXRVNQ-UHFFFAOYSA-N 0.000 title 1
FRUWMYWEARDNTC-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indole Chemical compound C1C=CC=C2NCCC21 FRUWMYWEARDNTC-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 454
150000003839 salts Chemical class 0.000 claims abstract description 105
238000000034 method Methods 0.000 claims abstract description 102
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 48
201000010099 disease Diseases 0.000 claims abstract description 45
125000000217 alkyl group Chemical group 0.000 claims description 665
-1 cyclodecyl Chemical group 0.000 claims description 400
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 248
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 193
125000000753 cycloalkyl group Chemical group 0.000 claims description 149
239000002585 base Substances 0.000 claims description 146
125000001072 heteroaryl group Chemical group 0.000 claims description 133
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 119
125000003118 aryl group Chemical group 0.000 claims description 113
125000003545 alkoxy group Chemical group 0.000 claims description 110
125000000623 heterocyclic group Chemical group 0.000 claims description 104
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 102
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 94
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 92
238000011282 treatment Methods 0.000 claims description 90
125000001424 substituent group Chemical group 0.000 claims description 82
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 77
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 71
239000000460 chlorine Substances 0.000 claims description 67
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 57
229910052757 nitrogen Inorganic materials 0.000 claims description 48
125000005843 halogen group Chemical group 0.000 claims description 46
125000003396 thiol group Chemical class [H]S* 0.000 claims description 43
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 42
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 41
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
206010028980 Neoplasm Diseases 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
201000011510 cancer Diseases 0.000 claims description 33
125000000468 ketone group Chemical group 0.000 claims description 28
239000007789 gas Substances 0.000 claims description 27
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 24
125000000392 cycloalkenyl group Chemical group 0.000 claims description 23
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 23
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 21
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
229960002449 glycine Drugs 0.000 claims description 21
125000003342 alkenyl group Chemical group 0.000 claims description 19
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
125000000304 alkynyl group Chemical group 0.000 claims description 18
230000004663 cell proliferation Effects 0.000 claims description 18
125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 15
125000004414 alkyl thio group Chemical group 0.000 claims description 14
229940067157 phenylhydrazine Drugs 0.000 claims description 14
239000002689 soil Substances 0.000 claims description 14
229930194542 Keto Natural products 0.000 claims description 13
150000001335 aliphatic alkanes Chemical class 0.000 claims description 13
GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 claims description 13
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 13
125000003226 pyrazolyl group Chemical group 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000002883 imidazolyl group Chemical group 0.000 claims description 12
150000002576 ketones Chemical class 0.000 claims description 12
150000002978 peroxides Chemical class 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 11
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
229910052707 ruthenium Inorganic materials 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
230000015572 biosynthetic process Effects 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
150000003254 radicals Chemical class 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
125000005368 heteroarylthio group Chemical group 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
235000013336 milk Nutrition 0.000 claims description 7
239000008267 milk Substances 0.000 claims description 7
210000004080 milk Anatomy 0.000 claims description 7
125000002971 oxazolyl group Chemical group 0.000 claims description 7
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims description 6
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
125000000524 functional group Chemical group 0.000 claims description 6
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 6
YKPQUSLRUFLVDA-UHFFFAOYSA-N $l^{2}-azanylmethane Chemical compound [NH]C YKPQUSLRUFLVDA-UHFFFAOYSA-N 0.000 claims description 5
IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 5
KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 claims description 5
239000005711 Benzoic acid Substances 0.000 claims description 5
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
239000005864 Sulphur Substances 0.000 claims description 5
235000010233 benzoic acid Nutrition 0.000 claims description 5
125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
238000006467 substitution reaction Methods 0.000 claims description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 3
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 3
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 claims description 2
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 2
GDSQTWDUCDSZEY-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-indazole Chemical compound C1CCCC2=C1C=NN2 GDSQTWDUCDSZEY-UHFFFAOYSA-N 0.000 claims description 2
KQBVVLOYXDVATK-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-indole Chemical compound C1CCCC2=C1C=CN2 KQBVVLOYXDVATK-UHFFFAOYSA-N 0.000 claims description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
241000196324 Embryophyta Species 0.000 claims description 2
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 claims description 2
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
238000002512 chemotherapy Methods 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 2
235000021286 stilbenes Nutrition 0.000 claims description 2
IKRJDNRUEIWOIB-UHFFFAOYSA-N trifluoromethylhydrazine Chemical compound NNC(F)(F)F IKRJDNRUEIWOIB-UHFFFAOYSA-N 0.000 claims description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 8
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 4
XVJMMRCIYPAAMO-UHFFFAOYSA-N 2-(2-hydroxyethylamino)benzamide Chemical compound NC(=O)C1=CC=CC=C1NCCO XVJMMRCIYPAAMO-UHFFFAOYSA-N 0.000 claims 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
150000001925 cycloalkenes Chemical class 0.000 claims 2
KAQVFEITQMBSEF-UHFFFAOYSA-N cyclopentyl methanesulfonate Chemical compound CS(=O)(=O)OC1CCCC1 KAQVFEITQMBSEF-UHFFFAOYSA-N 0.000 claims 2
125000004222 fluoren-1-yl group Chemical group [H]C1=C([H])C2=C(C([H])=C1[H])C([H])([H])C1=C(*)C([H])=C([H])C([H])=C21 0.000 claims 2
235000013905 glycine and its sodium salt Nutrition 0.000 claims 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 claims 2
HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 claims 1
IUGUPWHFLZEPHN-UHFFFAOYSA-N 1-prop-2-ynylpyrrolidine Chemical compound C#CCN1CCCC1 IUGUPWHFLZEPHN-UHFFFAOYSA-N 0.000 claims 1
UFLWECJWSGWVHB-UHFFFAOYSA-N 1H-carbazole Chemical compound C1=CC=C2C3=CC=CCC3=NC2=C1 UFLWECJWSGWVHB-UHFFFAOYSA-N 0.000 claims 1
ZOHGOQJROHLKIB-UHFFFAOYSA-N 1h-pyrazol-5-ylhydrazine Chemical compound NNC=1C=CNN=1 ZOHGOQJROHLKIB-UHFFFAOYSA-N 0.000 claims 1
KXPBYKQQPWQKCN-UHFFFAOYSA-N 2-(oxolan-3-ylamino)benzamide Chemical compound NC(=O)C1=CC=CC=C1NC1COCC1 KXPBYKQQPWQKCN-UHFFFAOYSA-N 0.000 claims 1
IJZYLBAJQAJKAG-UHFFFAOYSA-N 2-ethyl-5,5-dimethylcyclohexa-1,3-diene Chemical compound C1=CC(CC=C1CC)(C)C IJZYLBAJQAJKAG-UHFFFAOYSA-N 0.000 claims 1
VHEGELCKBUOCRB-UHFFFAOYSA-N 2-fluoro-6-[(4-hydroxycyclohexyl)amino]benzamide Chemical compound FC1=C(C(=O)N)C(=CC=C1)NC1CCC(CC1)O VHEGELCKBUOCRB-UHFFFAOYSA-N 0.000 claims 1
NNCLLCVOGHUVNC-UHFFFAOYSA-N 2-methylpyridin-1-ium-1-amine Chemical compound CC1=CC=CC=[N+]1N NNCLLCVOGHUVNC-UHFFFAOYSA-N 0.000 claims 1
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 1
PZHCRIKZVZKQOI-UHFFFAOYSA-N 4-(3-ethyl-6,6-dimethyl-4-oxo-5,7-dihydroindazol-1-yl)-2-fluoro-6-(oxolan-3-ylamino)benzamide Chemical compound C1=2CC(C)(C)CC(=O)C=2C(CC)=NN1C(C=1)=CC(F)=C(C(N)=O)C=1NC1CCOC1 PZHCRIKZVZKQOI-UHFFFAOYSA-N 0.000 claims 1
HNNNDEKVOJFVKK-UHFFFAOYSA-N 4-[3-(cyclopropylmethyl)-6,6-dimethyl-4-oxo-5,7-dihydroindazol-1-yl]-5-fluoro-2-[(2-hydroxycyclohexyl)amino]benzamide Chemical compound O=C1CC(C)(C)CC(N(N=2)C=3C(=CC(=C(NC4C(CCCC4)O)C=3)C(N)=O)F)=C1C=2CC1CC1 HNNNDEKVOJFVKK-UHFFFAOYSA-N 0.000 claims 1
241001385733 Aesculus indica Species 0.000 claims 1
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 1
102000016736 Cyclin Human genes 0.000 claims 1
108050006400 Cyclin Proteins 0.000 claims 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
VJBKFSFPQJTEQR-UHFFFAOYSA-N O1C(CCCC1)NC1=C(C(=O)N)C=CC=C1 Chemical compound O1C(CCCC1)NC1=C(C(=O)N)C=CC=C1 VJBKFSFPQJTEQR-UHFFFAOYSA-N 0.000 claims 1
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 claims 1
YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims 1
229960005164 acesulfame Drugs 0.000 claims 1
239000003905 agrochemical Substances 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
VKLUVISTQXQYPF-UHFFFAOYSA-N aminoazanium trifluoromethanesulfonate Chemical compound [NH3+]N.[O-]S(=O)(=O)C(F)(F)F VKLUVISTQXQYPF-UHFFFAOYSA-N 0.000 claims 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 claims 1
238000001354 calcination Methods 0.000 claims 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims 1
229960005286 carbaryl Drugs 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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TW097113864A 2007-04-16 2008-04-16 Tetrahydroindole and tetrahydroindazole derivatives TW200906394A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US91208307P	2007-04-16	2007-04-16
US1746907P	2007-12-28	2007-12-28
US1973208P	2008-01-08	2008-01-08

Publications (1)

Publication Number	Publication Date
TW200906394A true TW200906394A (en)	2009-02-16

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ID=39769290

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Application Number	Title	Priority Date	Filing Date
TW097113864A TW200906394A (en)	2007-04-16	2008-04-16	Tetrahydroindole and tetrahydroindazole derivatives

Country Status (9)

Country	Link
US (1)	US20080269193A1 (fr)
EP (1)	EP2146967A2 (fr)
JP (1)	JP2010524950A (fr)
AR (1)	AR066078A1 (fr)
CA (1)	CA2684240A1 (fr)
CL (1)	CL2008001069A1 (fr)
TW (1)	TW200906394A (fr)
UY (1)	UY31027A1 (fr)
WO (1)	WO2008130879A2 (fr)

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CN101955461B (zh) *	2010-10-08	2012-11-21	广州暨南生物医药研究开发基地有限公司	一种Hsp90抑制剂Xbj-B11及其制备方法与应用
EP2665711A1 (fr) *	2011-01-21	2013-11-27	Abbvie Inc.	Inhibiteurs picolinamides de kinases
AR088082A1 (es) *	2011-10-13	2014-05-07	Lilly Co Eli	Moduladores selectivos del receptor androgeno
US9738643B2 (en)	2012-08-06	2017-08-22	Duke University	Substituted indazoles for targeting Hsp90
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CN109796409A (zh) *	2019-01-31	2019-05-24	广州暨南生物医药研究开发基地有限公司	一种合成四氢吲唑化合物的方法

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2008
- 2008-04-14 WO PCT/US2008/060173 patent/WO2008130879A2/fr not_active Ceased
- 2008-04-14 US US12/102,128 patent/US20080269193A1/en not_active Abandoned
- 2008-04-14 CA CA002684240A patent/CA2684240A1/fr not_active Abandoned
- 2008-04-14 JP JP2010504173A patent/JP2010524950A/ja not_active Withdrawn
- 2008-04-14 EP EP08799842A patent/EP2146967A2/fr not_active Withdrawn
- 2008-04-15 CL CL200801069A patent/CL2008001069A1/es unknown
- 2008-04-16 UY UY31027A patent/UY31027A1/es not_active Application Discontinuation
- 2008-04-16 TW TW097113864A patent/TW200906394A/zh unknown
- 2008-04-16 AR ARP080101564A patent/AR066078A1/es unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101967125A (zh) *	2010-10-08	2011-02-09	广州暨南生物医药研究开发基地有限公司	一种Hsp90抑制剂Xbj-B16-1及其制备方法与应用
CN101967125B (zh) *	2010-10-08	2012-07-04	广州暨南生物医药研究开发基地有限公司	一种Hsp90抑制剂Xbj-B16-1及其制备方法与应用

Also Published As

Publication number	Publication date
EP2146967A2 (fr)	2010-01-27
JP2010524950A (ja)	2010-07-22
CL2008001069A1 (es)	2008-08-08
WO2008130879A3 (fr)	2008-12-18
WO2008130879A2 (fr)	2008-10-30
UY31027A1 (es)	2008-11-28
AR066078A1 (es)	2009-07-22
CA2684240A1 (fr)	2008-10-30
US20080269193A1 (en)	2008-10-30

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